Acetic Acid → alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactone

HRID 65263

Reaction equation

HRID 65263 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][O:12][C:10](=[O:11])[CH:9]2[CH2:14]OS(C)(=O)=O)=[CH:4][CH:3]=1.C(O)(=O)C.[SH-:24].[Na+]>C(O)C.C(OCC)(=O)C>[SH:24][CH2:14][CH:9]1[CH:8]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[CH2:13][O:12][C:10]1=[O:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 28015Sodium hydrosulfideHCID 13518915beta-(p-Chlorophenyl)-alpha-methanesulfonyloxymethyl-gamma-butyrolactone

Product 1

HCID 13518975alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactoneYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of α-methanesulfonyloxymethyl-β-phenyl-γ-butyrolactone (III) in 20 ml of ethanol were added 1.5 ml of acetic acid and then 1.2 g of commercially available 70% sodium hydrosulfide and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was diluted with 150 ml of ethyl acetate, washed with water in a conventional manner, dried over magnesium sulfate and the solvent was distilled off. The crude product thus obtained was purified by a column chromatography to give 400 mg (yield 52%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water in a conventional manner
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe crude product thus obtained
  6. customwas purified by a column chromatography

Sources & evidence

ORD record
ord-62844afc2adb4bd9bea5546d1bc4665b
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Linked notes

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